(S)-2-amino-N-((S,E)-5-phenyl-1-(phenylsulfonyl)pent-1-en-3-yl)propanamide

ID: ALA1242565

PubChem CID: 10384666

Max Phase: Preclinical

Molecular Formula: C20H24N2O3S

Molecular Weight: 372.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](N)C(=O)N[C@H](/C=C/S(=O)(=O)c1ccccc1)CCc1ccccc1

Standard InChI:  InChI=1S/C20H24N2O3S/c1-16(21)20(23)22-18(13-12-17-8-4-2-5-9-17)14-15-26(24,25)19-10-6-3-7-11-19/h2-11,14-16,18H,12-13,21H2,1H3,(H,22,23)/b15-14+/t16-,18-/m0/s1

Standard InChI Key:  PEGWSSHEIIFLNB-YARQWZEPSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -0.1784   -2.9174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2388   -3.6292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6481   -2.9112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7625   -4.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0480   -3.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3336   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0480   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3336   -4.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6191   -3.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9046   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -3.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9046   -4.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -5.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -6.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9077   -6.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9080   -7.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930   -7.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4762   -7.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4794   -6.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4757   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9514   -4.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6650   -5.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805   -4.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3778   -4.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6636   -3.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  6  8  2  0
 14 15  2  0
  4  5  1  0
 15 16  1  0
  6  9  1  0
 16 17  2  0
  3  2  2  0
 17 18  1  0
  9 10  1  0
 18 19  2  0
 19 14  1  0
  5  6  1  0
 11 20  2  0
 20  2  1  0
 10 11  1  0
  2 21  1  0
 21 22  2  0
 10 12  1  6
 22 23  1  0
  5  7  1  1
 23 24  2  0
 12 13  1  0
 24 25  1  0
  2  1  2  0
 25 26  2  0
 26 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1242565

   (S)-2-Amino-N-((S,E)-5-phenyl-1-(phenylsulfonyl)pent-1-en-3-yl)propanamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 372.49

Molecular Weight (Monoisotopic): 372.1508

AlogP: 2.44

#Rotatable Bonds: 8

Polar Surface Area: 89.26

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.99

CX LogP: 2.53

CX LogD: 1.84

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.74

Np Likeness Score: -0.19

References

1. Arastu-Kapur S, Ponder EL, Fonović UP, Yeoh S, Yuan F, Fonović M, Grainger M, Phillips CI, Powers JC, Bogyo M..  (2008)  Identification of proteases that regulate erythrocyte rupture by the malaria parasite Plasmodium falciparum.,  4  (3): [PMID:18246061] [10.1038/nchembio.70]

2. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

3. Shen XB, Chen X, Zhang ZY, Wu FF, Liu XH..  (2021)  Cathepsin C inhibitors as anti-inflammatory drug discovery: Challenges and opportunities.,  225  [PMID:34492551] [10.1016/j.ejmech.2021.113818]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data